1,2-Dichloroethane → Methyl 4-fluorobenzoate

HRID 1289754Notes

Reaction equation

HRID 1289754 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:12]CCl.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>CO>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 1118Sulfuric AcidHCID 99734-Fluorobenzoic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 67878Methyl 4-fluorobenzoateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-fluorobenzoic acid (25.0 g), 1,2-dichloroethane (120 ml), methanol (21.7 ml) and concentrated sulfuric acid (0.8 ml) was stirred for 16.5 hours with refluxing. After the reaction, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with chloroform, and washed with saturated brine. The mixture was dried over magnesium sulfate, and the solvent was distilled away under reduced pressure to give 23.0 g of a colorless transparent liquid (yield 84%).

Workup

  1. temperaturewith refluxing
  2. customAfter the reaction
  3. extractionextracted with chloroform
  4. washwashed with saturated brine
  5. dry with materialThe mixture was dried over magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-179e03524d2545d8bd6eeb287506228f
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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